YYZ - SXM

$158 Find Cheap Flights from Toronto to Simpson Bay - Compare and Save

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Everything you should know

Cheapest round-trip
$340
Typical prices: $377-$608
United Airlines
Wed 12/12Mon 12/24
YYZ - SXM • 1 stop
Cheapest non-stop
$348
Typical prices: $375-$601
Air Canada
Sat 12/8Sat 12/15
YYZ - SXM • Non-stop
Nonstop flights
You can fly direct with WestJet, Air Canada and Air Transat. Average duration is 4h 55m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 22% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $265 (round-trip)
Shortest trip • 8h 13m (one-way)
Insights
Insights
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We hope you love your trip to Simpson Bay!
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Expert advice
Flight Deals

Cheap Flights from Toronto to Simpson Bay (YYZ-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Simpson Bay

Sat, Dec 12 - Thu, Dec 24
United Airlines Logo
6:45 am - 3:57 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
8h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 pm - 7:59 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
27h 59m2 stops Washington, D.C. Dulles Intl Newark
$340United Airlines
Sat, Dec 12 - Mon, Dec 21
United Airlines Logo
6:45 am - 3:57 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
8h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 pm - 9:15 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
29h 15m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
$340United Airlines
Tue, Dec 8 - Tue, Dec 15
Air Canada Logo
9:55 am - 3:50 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
Air Canada Logo
4:50 pm - 9:10 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mnonstop
$348Air Canada
Mon, Jan 11 - Sat, Jan 16
WestJet Logo
9:30 am - 3:25 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
WestJet Logo
1:30 pm - 5:55 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$354WestJet
Sun, Dec 13 - Sun, Dec 20
American Airlines Logo
6:00 pm - 1:32 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
18h 32m1 stop Charlotte Douglas
American Airlines Logo
3:29 pm - 10:43 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
8h 14m1 stop Charlotte Douglas
$366American Airlines
Sat, Nov 28 - Sat, Dec 5
American Airlines Logo
6:00 am - 2:10 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
7h 10m1 stop Philadelphia
American Airlines Logo
5:33 pm - 11:59 amSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
19h 26m2 stops Miami Washington, D.C. Reagan-National
$368American Airlines
Mon, Jan 18 - Tue, Mar 2
WestJet Logo
9:30 am - 3:25 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
WestJet Logo
4:20 pm - 8:45 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$369WestJet
Tue, Mar 2 - Tue, Mar 9
Air Transat Logo
6:30 am - 12:15 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mnonstop
Air Transat Logo
1:25 pm - 5:50 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$369Air Transat
Tue, Dec 8 - Tue, Dec 15
Air Canada Logo
9:50 am - 3:45 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
Air Canada Logo
4:45 pm - 9:05 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mnonstop
$374Air Canada
Sat, Feb 27 - Tue, Mar 9
Air Transat Logo
6:30 am - 12:15 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mnonstop
Air Transat Logo
1:25 pm - 5:50 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$378Air Transat
Booking Insights

Price, demand and travel trends for Toronto Pearson Intl Airport to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Toronto Pearson Intl Airport to Simpson Bay?

Round-trip flights from Toronto Pearson Intl Airport to Simpson Bay typically range from $377 to $608. The lowest price found in the past 5 days was $340, on United Airlines.

What's the cheapest day of the week to fly from Toronto Pearson Intl Airport to Simpson Bay?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Toronto Pearson Intl Airport to Simpson Bay. It’s 9% cheaper than the average day, while Saturday is the most expensive, with prices 13% higher.

What’s the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay?

•June and October are the cheapest months to fly from Toronto Pearson Intl Airport to Simpson Bay at $375 round-trip.
•February ($552) and December ($533) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 47% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Toronto Pearson Intl Airport to Simpson Bay the cheapest?

Flights from Toronto Pearson Intl Airport to Simpson Bay are cheapest 12 weeks before departure. Booking in this window typically costs about 31% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Toronto to Simpson Bay

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet and Air Canada

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

John Walton

John Walton

Expert on Air Transat

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Key details for Toronto Pearson Intl Airport to Simpson Bay flights

Low season

September

Cheapest flight

$158
Beat the crowds with an average 61% drop in travelers.
The most popular month to fly with an average 66% increase in travelers.
One-way flight from Toronto Pearson Intl Airport to Simpson Bay

When to book flights from Toronto to Simpson Bay

Are your dates flexible? Find out the best times to travel from Toronto to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Toronto Pearson Intl Airport to Simpson Bay flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Toronto Pearson Intl Airport to Simpson Bay?

    These are the earliest and latest flight times available from Toronto Pearson Intl Airport to Simpson Bay:

    • Earliest: departs at 6:30 am and lands at 11:25 am
    • Latest: departs at 9:50 am and lands at 2:45 pm.

    The flight takes about 4h 55m.

  • What cabin classes can I book on flights from Toronto Pearson Intl Airport to Simpson Bay?

    Three cabin classes are available on flights from Toronto Pearson Intl Airport to Simpson Bay:

    • Economy Class
    • Premium Economy Class
    • Business Class

  • How long is a flight from Toronto Pearson Intl Airport to Simpson Bay?

    A nonstop flight from Toronto Pearson Intl Airport to Simpson Bay takes 4h 55m, covering 2,014 miles.

  • Do I need a passport to fly from Toronto Pearson Intl Airport to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Toronto Pearson Intl Airport to Simpson Bay flight?

    Round-trip flights from Toronto Pearson Intl Airport to Simpson Bay range from $377 to $608, with an average of $479 over the past 12 months. Anything below $377 counts as a good deal.

  • How expensive are last-minute Toronto Pearson Intl Airport to Simpson Bay flights?

    Last-minute fares on this route (booked within two weeks of departure) run 9% above the $479 route average. Book 12 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Toronto Pearson Intl Airport to Simpson Bay?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $265 round-trip via Chicago O'Hare Intl (ORD), compared to $473 for nonstop.

  • How does on-time performance compare across airlines flying from Toronto Pearson Intl Airport to Simpson Bay?

    Air Transat is slightly above the route average for timely arrivals, while WestJet has a lower on-time arrival rate. On-time arrival rates on Toronto Pearson Intl Airport to Simpson Bay flights are:

    • Air Transat: 85% on time
    • WestJet: 80% on time
    • Air Canada: 59% on time

    Overall, flights on this route are punctual 73% of the time on average.

  • What is the standard checked-bag allowance on flights from Toronto Pearson Intl Airport to Simpson Bay?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Toronto Pearson Intl Airport to Simpson Bay?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by WestJet and Air Canada. Other aircraft seen on the route include Airbus A321neo variants.

  • How are flight departures from Toronto Pearson Intl Airport to Simpson Bay spread across the day?

    Morning is the busiest departure period on Toronto Pearson Intl Airport to Simpson Bay flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Toronto Pearson Intl Airport to Simpson Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $340 to $2,195. That means the highest observed fare was about 6x higher than the lowest one.

  • Which airlines offer Wi-Fi on Toronto Pearson Intl Airport to Simpson Bay flights?

    Two airlines offer in-flight Wi-Fi on Toronto Pearson Intl Airport to Simpson Bay flights:

    • WestJet
    • Air Canada

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Toronto Pearson Intl Airport to Simpson Bay looking right now?

    One-way fares from Toronto Pearson Intl Airport to Simpson Bay are currently in line with typical prices for this route. Average one-way fares are about $244.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates averaging $40 for economy cars. Top options include:

    • Right Cars
    • Ace
    • Budget
    • Europcar
    • Alamo

  • Which airports can I use when flying from Toronto Pearson Intl Airport to Simpson Bay?

    Flights from Toronto Pearson Intl Airport to Simpson Bay usually depart from Toronto Pearson Intl (YYZ) and arrive at Simpson Bay Princess Juliana (SXM).

  • What time of day has the fewest delays on flights from Toronto Pearson Intl Airport to Simpson Bay?

    Afternoon flights have the fewest delays on this route, while morning departures tend to have the most.

  • At what point is a flight considered delayed from Toronto Pearson Intl Airport to Simpson Bay?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Toronto Pearson Intl Airport to Simpson Bay route, 27% of flights were delayed in the past 3 months, with delays averaging 1h 55m.

  • Which airports do connecting flights from Toronto Pearson Intl Airport to Simpson Bay pass through?

    One-stop flights from Toronto Pearson Intl Airport to Simpson Bay most commonly connect through:

    • Charlotte Douglas (CLT) - 25% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) - 25% of one-stop connections
    • Miami (MIA) - 20% of one-stop connections
    • Newark (EWR) - 10% of one-stop connections

  • Can I save money by using flexible dates for flights from Toronto Pearson Intl Airport to Simpson Bay?

    Yes. Flexible dates can save you up to 20% on flights from Toronto Pearson Intl Airport to Simpson Bay. Tuesday is the cheapest departure day at $440 round-trip on average, while Saturday is the most expensive at $546, a difference of $106.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Toronto Pearson Intl Airport to Simpson Bay?

    3 airlines operate flights between Toronto Pearson Intl Airport and Simpson Bay. The airlines offering nonstop flights on this route include:

    • WestJet
    • Air Canada
    • Air Transat

  • How much time can I save by choosing a different layover airport from Toronto Pearson Intl Airport to Simpson Bay?

    Flying via Newark (EWR) gives the shortest average 1-stop total travel time at 8h 13m, compared with 8h 13m via Atlanta Hartsfield-Jackson (ATL) and 8h 20m via Charlotte Douglas (CLT).

  • Which airlines offer extra legroom and free seat selection on Toronto Pearson Intl Airport to Simpson Bay flights?

    Among airlines operating Toronto Pearson Intl Airport to Simpson Bay flights:

    • WestJet: offers free seat selection
    • Air Canada: offers extra legroom; offers free seat selection
    • Air Transat: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Toronto Pearson Intl Airport to Simpson Bay flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • WestJet: a cabin bag and a checked bag in Economy Class
    • Air Canada: a cabin bag and a checked bag in Economy Class
    • Air Transat: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Toronto Pearson Intl Airport to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Saturday. On this route, Tuesday flights average $440, about $106 less than Saturday fares (19% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 31% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Toronto Pearson Intl Airport to Simpson Bay trip for June. Fares historically average $375 round-trip in that month - typically $177 less than the most expensive month, which is February (based on the last 12 months).
  • For the best chance of arriving on time, fly with Air Transat. Over the past three months, 85% of Air Transat flights from Toronto Pearson Intl Airport to Simpson Bay arrived on time, slightly above the route average of 73%. When flights on this route arrive late, they're delayed by an average of 1h 55m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through Chicago O'Hare Intl Airport (ORD) can be cheaper than flying direct. The cheapest layover option averages $265 round-trip on this route - about $208 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.

    • Simpson Bay Resort Marina & Spa
    • Hilton Vacation Club Flamingo Beach St. Maarten
    • The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

Prefer to fly direct from Toronto to Simpson Bay?

 
Find which airlines fly direct from Toronto Pearson Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Simpson Bay Princess Juliana

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

Air Canada,WestJet

Air Canada,WestJet

Wednesday

Air Canada,WestJet

Air Canada,WestJet

Thursday

WestJet

WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Transat,WestJet

Air Transat,WestJet

Sunday

Air Canada,WestJet

Air Canada,WestJet

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Toronto Pearson Intl

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

Air Canada,WestJet

Air Canada,WestJet

Wednesday

Air Canada,WestJet

Air Canada,WestJet

Thursday

WestJet

WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Transat,WestJet

Air Transat,WestJet

Sunday

Air Canada,WestJet

Air Canada,WestJet

See more direct flights

More options for your flight from Toronto to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental